Cesium fluoride → HCID 68543518, compound

HRID 30776Notes

Reaction equation

HRID 30776 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:29]=[CH:28][C:12]([O:13][CH2:14][CH2:15][NH:16][C@@H:17]([CH3:27])[C@@H:18]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[OH:19])=[CH:11][CH:10]=2)O1.Br[C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][C:33]=1[CH2:41][CH3:42].[F-].[Cs+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[CH2:41]([C:33]1[CH:34]=[C:35]([C:36]([OH:38])=[O:37])[CH:39]=[CH:40][C:32]=1[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][NH:16][C@@H:17]([CH3:27])[C@H:18]([OH:19])[C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)=[CH:28][CH:29]=1)[CH3:42]

Participants

8

Reactant 4

HCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 230907294-Bromo-3-ethylbenzoic acidHCID 68545025HCID 68545025, compound

Product 1

HCID 68543518HCID 68543518, compoundYield 23.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-((1R,2S)-2-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethylamino}-1-hydroxypropyl)phenol (0.04 g), 4-bromo-3-ethylbenzoic acid (0.044 g), tetrakis(triphenylphosphine)palladium (0.011 g), cesium fluoride (0.088 g), 1,4-dioxane (0.6 mL), ethanol (0.12 mL) and water (0.2 mL) was stirred at 140° C. for 5 min in a sealed tube. After being cooled to room temperature, the reaction mixture was purified by SCX ion exchange column chromatography (2 g, preconditioning: tetrahydrofuran, washing solvent:tetrahydrofuran, eluent:2 mol/L ammonia in methanol), followed by reverse phase column chromatography (Shiseido Capcell Pak C18 ODS, 5 μm, 120 Å, 20×50 mm, linear gradient 0.1% aqueous formic acid/acetonitrile=90/10-60/40) to afford the title compound (0.010 g) as a white amorphous. The structure and physical data were shown in table 3.

Workup

  1. temperatureAfter being cooled to room temperature
  2. customthe reaction mixture was purified by SCX ion exchange column chromatography (2 g, preconditioning: tetrahydrofuran, washing solvent:tetrahydrofuran, eluent:2 mol/L ammonia in methanol)

Sources & evidence

ORD record
ord-3b4921e1c8b54f71ab89045f4b1c68d9
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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